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Aromaticity and Other Conjugation Effects

ISBN: 978-3-527-32934-2
466 pages
September 2012
Aromaticity and Other Conjugation Effects (352732934X) cover image
The authors provide an excellent overview of conjugation effects in organic chemistry within and between Pi systems. Besides various
aspects of aromaticity one finds detailed discussions of homo-, spiroand hyperconjugation as well as effects of through-space and throughbond interactions. These effects are presented on the basis of experimental results and are analyzed by the use of qualitative arguments of perturbation theory and from a comparison with results from high level ab initio calculations.

This book is a must-have for bachelor students from the second year on, master and PhD students of chemistry. Also students in science
such as physics, biology and medicine will benefit from the concepts described in the book. Furthermore, chemists in research and development will be grateful to find here an overview of conjugation effects allowing to understand the structures, the dynamics and the reactivity of molecules.
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Foreword VII

Preface XIII

1 Conjugated π Systems 1

1.1 Linear Conjugated Polyenes 1

1.2 Conjugated Oligoalkynes 17

1.3 Conjugated Planar Monocyclic p Systems 22

1.4 Criteria for Aromaticity 28

1.5 Structures of Monocyclic (4nþ2)p and (4n)p Annulenes 46

1.6 Conjugated Polycyclic Planar p Electron Systems 62

1.7 Substituent Effects 75

1.8 Conjugation in Two and Three Dimensions 82

References 122

2 Through-Space Interactions between π Systems 133

2.1 Homoconjugation 133

2.2 Transannular Effects 135

2.3 Homoaromatic Systems 156

2.4 Spiroconjugation 166

References 176

3 DonorAcceptor Interactions between Planar Arenes 181

3.1 Donor-Acceptor Complexes 181

3.2 Structures of Benzene and Related Aromatics in the Solid State 187

3.3 Interactions between Molecules of Opposite Electric Quadrupole Moments 189

3.4 Model Studies to Measure the Strength of Non-Covalent Interactions Between p Systems in Organic Solvents 190

3.5 Model Calculations on p–p Interactions 196

3.6 Applications and Consequences of p–p Interactions of Arenes in Chemistry 201

References 213

4 Through-Bond Interactions between π Systems and Non-Bonded Electron Pairs of Heteroatoms 217

4.1 Theoretical Models 217

4.2 Dehydroaromatics 223

4.3 Through-Bond Interactions between Non-Conjugated p Systems 226

4.4 Rationalization of Intramolecular Reactivity by Through-Bond Coupling 265

References 279

5 Hyperconjugative Interactions 283

5.1 Concept of the Two-Electron/Two-Orbital Interactions 283

5.2 Definition and Manifestation of Ground State Properties 288

5.3 Positive Hyperconjugation (σ_p, σ_π*_ and σ _ σ * Interactions) 296

5.4 Negative Hyperconjugation (n_ σ * and π_ σ* Interactions) 329

References 356

6 Theoretical Models 361

6.1 Quantum Chemical Calculation Methods – An Overview 361

6.2 Orbital Interactions 396

6.3 Spectroscopic Methods for Detecting Conjugation Effects 409

References 426

7 Appendix 429

7.1 Character Tables for Selected Symmetry Groups 429

7.2 Basic Equations for Nuclear Magnetic Shielding in Molecules 436

Reference 438

7.3 Energy Conversion Table and Abbreviations 438

Subject Index 441

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Rolf Gleiter has been professor emeritus since 2005 and in 2011 was appointed senior professor of chemistry at the University of Heidelberg. He studied chemistry and completed his doctoral thesis under the supervision of F. Effenberger in Stuttgart in 1964. From 1965 - 1968 he carried out postdoctoral work in the USA, one year with P. v. R. Schleyer at Princeton and two years with Roald Hoffmann at Cornell. He qualified for university teaching (Habilitation) in the laboratory of E. Heilbronner in Basel in 1972 and moved one year later as a full professor to the TU Darmstadt. From 1979 - 2005 he was professor at the University of Heidelberg. His main areas of research have been intra- and intermolecular bonding properties which were studied by synthesizing model systems and through investigations of their interactions by physical measurements supported by quantum chemical calculations. This work resulted in the synthesis of novel cyclophanes, cyclic oligoacetylenes, strained hydrocarbons and vicinal polyketones, and has led to various awards and honorary degrees.

Gebhard Haberhauer is Professor for Organic Chemistry at the University of Duisburg-Essen. He studied chemistry at the Universities of Vienna and Heidelberg and received his Ph.D. from the University of Heidelberg under the supervision of R. Gleiter. From 1999 - 2000 he was a postdoctoral fellow in the laboratory of J. Rebek, Jr. at The Scripps Research Institute in La Jolla. After working one year at BASF in Ludwigshafen, he returned to the University of Heidelberg, where he qualified for university teaching (Habilitation) from 2001 to 2005 under the mentorship of R. Gleiter. In 2005, he was appointed Professor for Organic Chemistry at the University of Duisburg-Essen. His current research interests include chirality induction with azole-containing cyclopeptides and the synthesis of molecular switches and motors.
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